Fear of the unknown, a false sense of obligation, or indecision are but a few of the influences that can subjugate ambitions and dreams to the stress of starting over after a career in the service.  It doesn’t have to be that way.  This is a veteran-focused post to help others work through their fears of the unknown as they prepare for post-military life, but it applies to anyone who is considering a mid-life career change.

Retiring from the armed forces, or from any long career, can be a very stressful transition as you let go of the past and face an uncertain future. Unfortunately, there is no crystal ball to guide you, but one of my new favorite quotes is from Abraham Lincoln – “The best way to predict your future is to create it.”  Sounds easy enough, but for military member in particular, it’s hard to just walk away from years of institutionalization.  To be sure, service members often have strong networks built over the course of their time in the military, and these networks can be invaluable during the search for post-service employment.   However, as useful as these networks are, they are also apt to keep you from branching out into something new, or taking time off to pursue uncharted possibilities.  As a result, it is easy to fall into a trap where income becomes the driving force behind career decisions rather than a deep introspective look into what you really want for a “second life.”  This leads to a pursuit of employment rather than fulfillment, and ends in a contract that forces you to trade more precious time for money.  If you are shackled to a life dictated by consumerism and workism, your “one day” list becomes less and less achievable.  This is paradoxical, because chances are you might secure a decent salary on top of your retirement income, but there is no guarantee you will have time for anything on your bucket list of dreams and ambitions.  After giving so much to your country, and asking your families to sacrifice just as much or more, taking time to reconnect with them and yourself before a second career is worth contemplation.  Perhaps just as important, this will give you some “maneuver space” to sort through the stress, the noise, and the pressure of starting anew.  That space might be a few months, or it might be a few years, but either way it is time well-spent.

Consider the following as you prepare for your post-military life:

• Military service didn’t leave much room for hobbies and passions.  Do you have any languishing in the recesses of your life?
• Military regulations and culture compelled you to identify yourself by an all-consuming job title, which in turn suppressed your identity as an individual.  You were the Admiral, the Colonel, Skipper, Warrant, Chief, Senior, Top, OPSO, COS, the LPO, the First Sergeant.  Do you really know who you are anymore without a job title to define you? 
• Time keeps ticking, but money comes and goes.  Is time more valuable than money when you realize that you can bank one but not the other?

As you contemplate those lost dreams, you might be asking yourself with a twinge of frustration, “Why didn’t I go for it?  What was I afraid of?  What was the worst thing that could have happened to me if I had unshackled myself from the ‘golden handcuffs,’ put down the electronic tether, and lived the life I always imagined?”  You might be surprised to learn the worst thing that could have happened was nothing from which you could not have quickly recovered. 

Rewind to the present.  Ask yourself this question, “Have I ever allowed myself to fail?”  If you made it all the way through a 20-year (or more) career, chances are the answer is a resounding no!  So why do you think you will start failing now?  I’ll let you in on a little secret…you won’t.  You already know how to succeed.  The sad truth, however, is that many of us never take a chance, because we focus on the reasons we shouldn’t…the fears…rather than the reasons we should.  But what are you afraid of? 

Every military member goes through transition class on their way out of the service.  You learn that it is possible to reinvent yourself, but it isn’t easy.  You are instructed to make a list of your assets, your liabilities, and any gaps you have in your skill set, then cross reference it against what you need to break in to a sector outside of what you have been doing for the past twenty plus years.  You are told to be willing to move to an area where that sector has a presence, be patient, be willing to evangelize yourself, build a network in your new community, use your hard-earned benefits to get the education or certifications you need to fill in any gaps, and be willing to start at the bottom.  If you do these things while exhibiting all the qualities that made you successful on active duty, you will succeed.  

What if I told you that same blueprint for reinventing yourself professionally is just as useful for reinventing yourself personally, and going after those “one day” dreams before you blindly (or deliberately) trade one overlord for another.  With a little bit of planning and foresight, you can do it, and if I haven’t made my position clear, I think you should.  When else will you get a planned break in your professional life to do something crazy?  

I started my transition playing by the rules.  I spent many hours working on a resume. I went to career fairs.  I interviewed for jobs.  I received job offers.  None if it felt right in my gut.  I started terminal leave in June 2018 in a panic stricken state, grasping for a lifeline.  At my wife’s urging I had been exploring the idea of trade school using my GI Bill benefits, but I was afraid to commit.  “It’s not what I am expected to do,” was my typical reason, which was ridiculous.  I was afraid of the unknown and everything that came with it.  That was the truth.  I had reached the first portal of fear, and with my wife’s encouragement, I stepped through it.  

In September 2018 I enrolled in a six-month program at the IYRS School of Technology and Trades in Newport, RI that ended with a one-month internship and American Boat and Yacht Council (ABYC) certifications as a Marine Electrician, Diesel Mechanic, and Systems Technician.  I wrote about how beneficial that was for me as a veteran while I was serving as a student ambassador at the school.  But as I approached the end of the program I realized I had only deferred my dilemma.  I still had to figure out my life after the military.

Once again, I found myself grasping for the familiar and hiding from my fears.  I applied for a government job overseas knowing it wasn’t what I really wanted.  A friend was recruiting me to come back to the staff I had left a year and a half earlier, but after I submitted my resume there were knots in my stomach.  “What am I doing,” I asked myself.  “Is this what I really want?”  I wasn’t ready for staff meetings and point papers again.  I wasn’t ready for days when I went to work at dawn and came home after dinner just to get up and do it all over again while my life ticked away a second at a time. 

My wife had a dream that we could sell it all and go sailing.  I was adamantly opposed.  “If there is one thing I learned at the marine trade and technology school,” I joked, “it is don’t buy a boat!”  The truth of the matter is I was terrified of selling everything and buying a boat.  There were too many voices in my head telling me it would be our ruination…MY ruination.  I hid behind my biggest fear – money.  We couldn’t afford it.  End of story. 

But, it wasn’t.

 It’s amazing what you can accomplish when you put your mind to it.  As I tell my children, there is a solution to every problem, we only need to outthink it.  So we looked at the problem again and realized we could afford it.  But, I still wasn’t ready to commit.  I needed a push.

Fate intervened on my behalf.  Much to my surprise, my resume never made it through the initial screening for the civil servant position so I never got the job interview on the staff overseas.  Despite my ego being bruised, I actually breathed a sigh of relief.  I was a free man again.  A few weeks later after some long, introspective conversations with my wife, I agreed to the sailing adventure.  Failure had somehow opened a pathway to an outcome I did not think possible.  That was in March 2019.  Four months later we would be boat owners after an exhausting push to sell, donate, or repurpose just about everything we owned.  Three months after that we would be be getting underway from Hampton, VA for a 1,600 nautical mile ocean passage to Antigua.

How did we go from “normal life” to “boat life” so quickly?  We followed the same blueprint I received in the transition seminar.  We laid out a plan, prioritized our resources, and focused everything we had on the achievement of our goal.  I had already filled in the knowledge gaps by becoming a certified marine mechanic.  Anyone who knows boats will tell you that 90% of boat ownership is boat maintenance, so I felt confident I could handle that responsibility with my new skills.  I grew up sailing so that wasn’t an issue, but living aboard a boat full-time was another story.  We hired a couple who had twice circumnavigated with their kids as “cruising coaches.”  We built a network by talking about our plans with people who could help and guide us.  We made sure we were able to fund our dream by paying cash for a boat and living within the means of my retirement income.  Using our new and growing network we found a boat, brokered the deal, and moved aboard on July 31, 2019.   

It was not an easy transition from land life to sea life.  In fact, it was harder than anything we had ever done. Being a military family, we were used to relocating and starting over every couple years, so we put all that experience to good use.  But, this time it was different.  It was all on us to get it done.  There were at least three distinct points when we wanted to quit.  We didn’t, largely due to the encouragement and instruction we received from our cruising coaches plus other people who had walked the same path.  The rewards for persevering are too many to list.  Suffice it to say, I answer to no master.  I have learned more about myself and my family in six months than I have in six years.  I have swum with a whale in 19,000 feet of water halfway between Bermuda and the Leeward Islands.  We have sailed our way through 50-knot squalls and come out the other side stronger and more resilient.  I have made lifelong friendships with people I never would have met had I stayed in my “safe” bubble.  I have gained valuable perspective by using this time away from the rat race to sort myself; to be a better husband, father, and friend.

I certainly thought it was.  But for me, at least, it wasn’t.  I am not getting any younger.  The counterargument doesn’t hold up in my opinion.  You can always get a job and make money, but you can’t make more time.  Another aspect of this counterargument is that your network will abandon you if you take time for yourself and family.  I also believe that this is invalid, and would go so far as to suggest that the network you built while in the service will respect you more for taking some time to sort yourself.  Some might even find inspiration from your example.

We as Americans have it all backwards.  We work and work and work until we hit the “golden years,” then we retire with the idea that we are going to take off from our empty nest and explore the world.  I have heard so many tragic stories about people who FINALLY get some time to do the things they have always wanted to do only to be sidelined by unexpected health crises that leave them debilitated or worse.  Derek Thompson, a senior staff writer for The Atlantic wrote a compelling article in February 2019 titled, “Workism is Making Americans Miserable,” where he argues that work has become, unfortunately, the, “centerpiece of one’s identity and purpose.”  It’s an excellent, thought-provoking read.

Work, pay taxes, then die.  

As a retiring military member you have the resources to do what you want – healthcare, education opportunities, steady income, and many more benefits to jumpstart your second life.  You only need to face down your fears and embrace the possibilities that lay before you.  I am not done working, but I guarantee whatever employment I pursue in the future will be far different than what I thought I had to shoehorn myself into when I first transitioned from service.  We have had a lot of people tell us how amazing our life is…how lucky we are…how courageous we are to be out sailing with our kids full time.  We don’t see ourselves as different or special.  We are just us, living a life of our choosing.  We realized in hindsight that fear had been holding us back, not resources.  Once we made our decision, we were flabbergasted by how everything suddenly seemed to align behind us.  It was all there to begin with, but we were blinded by our fears of the unknown, and therefore too afraid to take a chance. 

Fear is paralyzing, and in the weeks surrounding my transition there were days when I didn’t want to get out of bed and face reality.  In the middle of those dark moments, a very wise friend of mine asked me to stretch my hands out in front of myself palms up, then she had me clench my fists.  She looked at me and said, “There won’t be room for anything new in your life if you are holding onto everything so tightly, afraid to let go.  You have to open your hands and be willing to release – toxic relationships, needless possessions, clutter, the wrong career, convenience, the safe and easy path, money.  But more importantly, you have to open you hands so what you really want has a place to land.”  

I stood there for a moment clenching and unclenching my upturned hands.  I am not a particularly spiritual person, but I was shocked at how profoundly her simple exercise struck a chord.  “Money comes and money goes, and it should,” she concluded, ”but even though we have had our backs to the wall a number of times, we always believed we would be fine because we kept our hands, figuratively of course, upturned and open.”  She and her husband are better now than ever after launching their own business nearly twenty years ago.  They had been let go from their previous jobs at the same time, when their kids were still young and their stress levels already high.  In that moment of darkness, they chose to open their own business and live life according to their own terms.  It wasn’t easy, but looking back they wouldn’t want it any other way.  

In the final analysis, it’s not about how much you have, but what you do with it.   Achieving your ambitions means making decisions, prioritizing and leveraging resources, and aligning efforts.  Do you want to be linked in right away,  or checked out to gain some perspective and clarity?  The choice is yours, and it doesn’t matter how big your proverbial or actual boat is.  It only matters that you believe in yourself and face down your fears.  Trust me, someone always has a bigger boat, and the size of yours doesn’t matter. You can find dozens of YouTube channels where people are sailing the world on every manner of boat imaginable.  I used to watch some of them and say, “Look at their boat.  It’s so ugly, or small, or dilapidated.” My wife would answer, “Yeah, sure is…but they are doing it!”  How true.  Would you rather be sitting in a staff meeting wishing you were doing it, or actually doing it?  

I’ll close with this final thought.  Many, if not all of us, who are retiring from a career in the service lost shipmates, close friends, and comrades in training and combat.  A few years ago, standing on a beach in Italy looking out into the Adriatic Sea, where a friend in Air Wing 17 had perished during a nighttime training flight off the USS George Washington (CVN-73) in 2002, I made a promise that if I somehow made it through my military career, I would not squander the opportunity to fulfill dreams and live an amazing life.  I felt like I owed that to those who couldn’t.  Life is short, and precious.  Don’t let fear hold you back.  Don’t let a false sense of obligation keep you from doing the things on your “one day” list.  If you do, that list will go unfulfilled.